C(sp3)–F reductive elimination from alkylgold(iii) fluoride complexes
Authors:
- 13 October 2011
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Science
- Vol. 3 (1) , 72-76
Abstract
Rare examples of C(sp3)–F reductive elimination were observed from several cis-F2Au(R)(IPr) intermediates generated by oxidation of (IPr)AuR complexes with XeF2 . For R groups bearing β-hydrogens, β-hydride elimination was competitive with C(sp3)–F reductive elimination. For strained cyclic R groups and most acyclic R groups lacking β-hydrogens, carbocation-like rearrangements occurred prior to C(sp3)–F reductive elimination. Kinetics of the decay of one cis-F2Au(R)(IPr) species, stereochemical analysis of reductive elimination with a chiral R group, and DFT analysis collectively suggest C(sp3)–F reductive elimination proceeding through transient cationic [(IPr)Au(F)(R)]+ intermediates with significant ionization of the Au–alkyl bonds.Keywords
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